Dimethylformamide dimethyl acetal → 1-(3,4-Dimethoxybenzyl)-5-[4-methoxy-3-(2-methoxyethoxy)phenyl]-4-oxo-1,4-dihydro-pyridine-3-carbonitrile

HRID 506156노트

반응식

HRID 506156 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=[O:14])[CH2:11][C:12]#[N:13])=[CH:5][C:4]=1[O:15][CH2:16][CH2:17][O:18][CH3:19].[CH3:20][N:21]([CH:23](OC)OC)[CH3:22].[CH3:28][O:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][C:37]=1[O:38][CH3:39])CN>CN(C=O)C.C1(C)C=CC=CC=1>[CH3:28][O:29][C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][C:37]=1[O:38][CH3:39])[CH2:23][N:21]1[CH:20]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[C:4]([O:15][CH2:16][CH2:17][O:18][CH3:19])[CH:5]=2)[C:10](=[O:14])[C:11]([C:12]#[N:13])=[CH:22]1

참가 물질

6

반응물 3

HCID 78373Dimethylformamide dimethyl acetalHCID 79832VeratrylamineHCID 684663014-[4-Methoxy-3-(2-methoxyethoxy)phenyl]-3-oxo-butyronitrile

생성물 1

HCID 684663701-(3,4-Dimethoxybenzyl)-5-[4-methoxy-3-(2-methoxyethoxy)phenyl]-4-oxo-1,4-dihydro-pyridine-3-carbonitrile수율 55%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To a stirred solution of 4-[4-methoxy-3-(2-methoxyethoxy)phenyl]-3-oxo-butyronitrile (9.91 g, 34.5 mmol) in 20 mL of anhydrous DMF was added DMF-DMA (20.2 mL, 152 mmol). The resulting mixture was heated at 100° C. for 15 h and was concentrated in vacuo. The crude material was mixed with 3,4-dimethoxybenzylamine (0.687 mL, 41.4 mmol) in 20 mL of anhydrous toluene and the mixture was heated at reflux for 2 h. The reaction mixture was cooled, concentrated in vacuo, and purified by flash chromatography on silica gel eluting with gradient 50-100% EtOAc/hexane to yield 8.5 g (55% yield) of 1-(3,4-dimethoxybenzyl)-5-[4-methoxy-3-(2-methoxyethoxy)phenyl]-4-oxo-1,4-dihydro-pyridine-3-carbonitrile as a yellow/orange foam.

후처리

  1. concentrationwas concentrated in vacuo
  2. temperaturethe mixture was heated
  3. temperatureat reflux for 2 h
  4. temperatureThe reaction mixture was cooled
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography on silica gel eluting with gradient 50-100% EtOAc/hexane

출처 및 근거

ORD 기록
ord-a51038d2f2984f7fb5184d3d610c1367
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07781591B2

반응 노트

불러오는 중…